Reacción #43379

ord-85ce16b4205a42c8bd3450e8ff110de5

Ecuación de reacción

O=C(O)c1ccc(Br)s1
5-bromo-thiophene-2-carboxylic acid
O=S(Cl)Cl
thionyl chloride
CC(C)(C)OC(=O)C(C)(C)N.Cl
tert.-butyl 2-amino-isobutyrate hydrochloride
O
water
CC(C)(C)OC(=O)C(C)(C)NC(=O)c1ccc(Br)s1
tert.-butyl 2-[(5-bromo-thiophen-2-yl)-carbonylamino]-isobutyrate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe mixture is then evaporated down i
  2. 2
    Otroevaporated down completely
  3. 3
    workup.ADDITIONThe residue is added dropwise to 10 ml dichloromethane
  4. 4
    workup.STIRRINGstirred for 16 h
  5. 5
    Extracciónextracted with dichloromethane
  6. 6
    Secadothe combined organic phases are dried over magnesium sulphate
  7. 7
    Otroevaporated down i

Procedimiento

2.63 g (12.3 mmol) 5-bromo-thiophene-2-carboxylic acid are refluxed in 15 ml dichloromethane together with 7.0 ml of thionyl chloride for 2 h with stirring. The mixture is then evaporated down i. vac. and the residue is twice taken up in toluene and evaporated down completely i. vac. The residue is added dropwise to 10 ml dichloromethane with stirring at ambient temperature in a mixture of 2.41 g (12.3 mmol) tert.-butyl 2-amino-isobutyrate hydrochloride in 20 ml dichloromethane with 5.14 ml (36.9 mmol) TEA and stirred for 16 h. The mixture is poured into water and extracted with dichloromethane, the combined organic phases are dried over magnesium sulphate and evaporated down i. vac.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07732466B2uspto-grants-2010_06